Resorcinol → 4-Cyclohexylresorcinol

Temperature

125 °C

Resorcinol (2.2 g, 20 mmol) and cyclohexanol (6.33 ml, 6 g, 60 mmol) were suspended in 85% polyphosphoric acid (8 ml). The mixture was heated to 125° C. for 24 hours, after which time TLC appeared to show complete consumption of the starting materials. On cooling the mixture was partitioned between water (50 ml) and diethyl ether (50 ml). The aqueous layer was discarded, and the organic portion extracted with sodium hydroxide solution (2×50 ml, 2M). The base extract was washed with ether (3×50 ml), and then acidified with aqueous hydrochloric acid (120 ml, 2M). The organic components were then extracted into diethyl ether (2×50 ml), dried (magnesium sulfate), filtered and the solvent removed under reduced pressure. The resulting brown oil was then chromatographed on silica gel, eluting with ethyl acetate/petroleum ether (bp 60-80° C.) 1:2 to give the desired product as an off-white solid (1.7 g, 44%).

1. customconsumption of the starting materials
2. temperatureOn cooling the mixture
3. customwas partitioned between water (50 ml) and diethyl ether (50 ml)
4. extractionthe organic portion extracted with sodium hydroxide solution (2×50 ml, 2M)
5. extractionThe base extract
6. washwas washed with ether (3×50 ml)
7. extractionThe organic components were then extracted into diethyl ether (2×50 ml)
8. dry with materialdried (magnesium sulfate)
9. filtrationfiltered
10. customthe solvent removed under reduced pressure
11. customThe resulting brown oil was then chromatographed on silica gel
12. washeluting with ethyl acetate/petroleum ether (bp 60-80° C.) 1:2

ORD record

ord-9ba61a208c2a4d5485a218ac3ac642f5

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06132740